Sodium Hydroxide → 5-methyl-3,6-dihydro-2H-pyran-2-carboxylic acid

HRID 1808006Notes

Reaction equation

HRID 1808006 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH:10]=[C:9]([CH3:12])[CH2:8][O:7]1)=[O:5])C.[OH-].[Na+]>CO>[CH3:12][C:9]1[CH2:8][O:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 597523065-methyl-3,6-dihydro-2H-pyran-2-carboxylic acid ethyl ester

Product 1

HCID 553027505-methyl-3,6-dihydro-2H-pyran-2-carboxylic acidYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-methyl-3,6-dihydro-2H-pyran-2-carboxylic acid ethyl ester (140 mg, 0.823 mmol) in MeOH (3.5 mL) and 10% aq. NaOH (1.0 mL, 2.5 mmol) was heated at 65° C. for 3 h, reaction mixture was cooled to room temperature, solvent was evaporated, diluted with water. The aqueous solution was washed with ether, and acidified with aq. 1 N HCl, extracted with ether. The ethereal solution was washed with brine and dried. Evaporation of the solvent furnished 5-methyl-3,6-dihydro-2H-pyran-2-carboxylic acid (82 mg, 70% yield. NMR 1H (CDCl3, 400 MHz): 5.54-5.5 (m, 1H), 4.24-4.1 (m, 3H), 2.4-2.3 (m, 2H), 1.6 (s, 3H).

Workup

  1. customreaction mixture
  2. customsolvent was evaporated
  3. additiondiluted with water
  4. washThe aqueous solution was washed with ether
  5. extractionextracted with ether
  6. washThe ethereal solution was washed with brine
  7. customdried
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-5f8c723d43914b6a873147e142e85692
Source dataset
uspto-grants-2013_01
Patent number
US08357718B2

Reaction notes

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